Amido-amide derivatives of dibasic acids and processes of preparing the same



Patented Sept. 2, 1952 ACIDS AND PROCESSES THE SAME OF PREPARING HermanB. Goldstein, Cranston, and Stanley T. Clary, Coventry, It. I.,assignors to Sun Chemical Corporation, Long Island City, N. Y., acorporation of Delaware No Drawing. Application October 5, 1949, SerialNo. 119,756

14 Claims. 1

The present invention relates to new organic compounds which arevaluable as assistants in the treatment and finishing of textilematerials.

One object of the present invention is to provide new water dispersibleorganic compounds useful for the treatment "of textile materials "which,upon such treatment, impart a highly improved hand and enhanced texturethereto.

Another object fof the presentinvention is to provide new waterdispersible organic compounds which are substantive to textile-materialsand which are highly resistant to ordinary laundering and dry' cleaningmethods afterapplication thereto, therebyimparting a relativelypermanent finish to suchtreated textiles.

Another'object of the present invention is to provide new-waterdispersible textile finishing agents which do not cause discolorationnor yellowing of textile materials treated therewith, Whichare effectiveover long periods of time and under all the ordinary operations andconditionsto which such textiles are subject, and which do not efi'ectany color change in the shade of dyed fabricsgnorwhichdeleteriouslyaffect the light fastness of dyestiifisi Otherobjects of the presentinvention will be apparent from the following description and appendedclaims.

It has been-'f'ound-jtha t the above objects may be accomplishedand-Ithat organic compounds having the properties and characteristicsdescribed thereinmay be prepared by reacting a high molecular weightaliphatic carboxylic acid, or derivativesthere'of, such as the esters orhalides thereof, with a polyamine to form an amide amine of such acid,and thereafter reacting the resultant amido amine with a dibasic acid,or a derivative thereof, such as the anhydride, esters -or acyl halidesthereof, in such manner that a disubstituted derivative of the dibasicacid is formed.- I

The organic compounds formed according to the process of the presentinvention may be considered to be disubstituted amido-amide derivativesof dibasic acids. Similarly, these products may also be considered to beacyl amides of a dibasic acid and high molecular weight aliphaticcarboxylic'acids. I 7

The high molecularweight aliphatic carboxylic acidsemployed in preparingthe above mentioned amido amines are those containing at least sixcarbon atoms in the aliphatic chain, as for example, caproic acid,caprylic acid and capric acid, and preferably those containing at leasttwelve carbon atoms in the'molecule, Among those acids 2 which arepreferred for use in the present invention are the higher saturatedfatty acids such as lauric acid, myristic acid, palmytic acid, stearicacid, animal and vegetable oil saturated fatty acid compositions such ascoconutfatty acids, and hydrogenated fatty acid compositions,

' such as from hydrogenated fish oils, hydrogenated cotton seed oil,hydrogenated soy bean oil and hydrogenated peanut oil. The higherunsaturated fatty acids as, for example, oleic acid, palmitoleic acid,linoleic acid, linolenic acid and eleostearic acid, may also be employedin preparing the compounds of the present invention. However, the use ofsuch acids is notpreferred since the end product, that is, the softenercompound, displays a tendency toward slight. discoloration due to theunsaturation in the finished product.

The polyamines which are reacted with the above mentioned acids toprovide the amido amines which may be subsequently reacted with adibasic acid to provide the new organic compounds of the invention,comprise those polyamines containing at least two amino groups of theprimary or of thesecondary type,and which may contain one or morealiphatic residues in the molecule. Examples of such polyamines includethe diamines such as ethylene diamine, trimethylene diamine,tetramethylene diamine, pentamethylene diamine, and hexamethylenediamine; the polyethylenejpolyamines such as diethylenetriamine,triethylene tetramine, tetraethylene pentamine, etch; substituteddiamines such as ethyl ethylene diamine, hydroxyethyl ethylene diamine,N-N'dihydroxyethyl ethylene diamine, N-ethyl N'- aminoethyl ethylenediamine; and such other polyamines as diamineethyl ether anddiaminoethyl thioether.

Polyamines of the type exemplified above may be reacted with any of'thepreviously mentioned aliphatic carboxylic acids to provide an amido,

acid, adipic acid, pimelic acid,- suberic acid and 'sebacic acid; theunsaturated aliphatic dicarboxylic acids such as maleic and fumaricacids; cyclic aliphatic dicarboxylic acids such as 1-4. cyclohexanedicarboxylic acid; and aromatic and alkyl aromatic dicarboxylic acidssuch as phthalic acid, isophthalic acid, homophthalic acid, and uviticacid. Other dibasic acids, substituted or interrupted in their structureby hydroxyl, ester, ether and amino groups, or by halogen, oxygen andsulfur atoms may also be employed in the present invention- Some suchacids are malic acid, tartronic acid, tartaric acid, l chlorophthalicacid, DL bromobutanedioic acid, aspartic acid, diglycolic acid, anddithioglycolic acid. The anhydrides, esters and acyl halides oi theabove mentioned dibasic acids may also be employed in carrying out theinvention.

The compounds obtained in accordance with the procedures hereinafteroutlined and with the materials above set forth may be represented bythe following general formula:

i) R; R3

In the above formula R1 and R7 represent an aliphatic chain containingfive or more carbon atoms. Furthermore R1 and R7 may be identical orthey may be different, depending upon whether the radicals representedby El and R1 are derived from the same acid or from diiferent acids.

R2, R3, R5 and Rs may represent hydrogen, a lower alkyl radical, or alower hydroxyalkyl radical, the various substituents corresponding tothe terminal substituents occurring in the particular polyamineemployed.

Re and R5 may further represent an acyl residue of an aliphaticcarboxylic acid. The particular compounds in which R3 and R5 have suchrepresentation occur, for example, in an amide amine in which thepolyamine has been so reacted with an aliphatic carboxylic acid thatboth terminal amino groups contain an acyl radical and in which at leastone of the acyl substituted. amino groups contains a free hydro-genatom.

Depending upon the particular polyamine employed in preparing the amideamine, G in the above formula may be a secondary amino group, a simplelower alkyl or lower alkylol substituted amino group, oxygen or sulfur.

The letters a, b, c, d, e and ,1 represent integers, a and 0representing integers from 0 to 6; and b, d, e and 1 representingintegers from 1to6.

That portion of the above general formula represented by X is adicarboxylic acid residue in which R4 may represent an aliphatic group,a cyclo aliphatic group, an aromatic group or an alkyl aromatic group.R4 may also represent any of the said groups substituted within theirstructure by halogen, oxygen, and sulfur atoms, or by amino, ester,hydroxyl, and ether groups, or any of the said groups in which thecarbon linkage is interrupted by halogen, oxygen or sulfur atoms, or byan amino, ester, hydroxyl; or ether group.

As has been set forth above, X in the general formula represents adicarboxylic acid residue.

* The linkage between the two carbonyl groups contained in the saiddicarboxylic group need not necessarily be interrupted by any of thegroups represented by R4 but may be a simple linkage such as is had inoxalic acid. This type of linkage is obtained when oxalic acid isemployed as the dibasic acid in the reactions set forth in the presentinvention. The resultant compounds therefore correspond to the generalformula tion, as represented by the above illustrative formulas areprepared by reacting between approximately one mol to two mole of analiphatic carboxylic acid containing at least six carbon atoms in thealiphatic chain with approximately one mol of a polyamine of the typepreviously described v at a temperature between approxi mately l5ll-l80C. until substantially complete reaction is obtained, and thereafteradding approximately one-half mol of a dibasic acid and further reactingthe admixture at a temperature between approximately -210 0., de-

pending upon the particular reaction materials employed, untilsubstantially complete reaction is secured as evidenced by therelatively low amine value of the reaction product. The productsobtained in this. manner, when cool, are generally tan colored, wax-likematerials which are at least. partially dispersible in hot water. Inorder to insure complete aqueous dispersion of the products of thepresent invention, it is generally preferable to add a solubilizingagent thereto, such as a lower alcohol, or a peptizing agent, such as analkali, organic acid, a soap, etc.

Where the amido amine which is to be reacted with a dibaslc acidcontains more than one amino group in the molecular chain, more than onedicarboxylic acid residue may be introduced into the structure of thecompound by increasing the molecular quantity of the dibasic acid inproportion to the. molecular amount of the amido amine to be reacted.Thusly, where the symbol a and c in. the above illustrative formulae areat least one and where G represents a secondary amino group, a seconddicarboxylic acid residue may be incorporated into the structure of thecompound, linking at least two of the amino groups represented by G. Oneexample of such a compound and a method whereby the same is obtained arehereinafter set forthin illustrative Example 3.

The compounds of the present invention may be worked up into aconcentrated, water soluble softener paste, by treatment of the samewith low molecular organic acids such as formic, acetic propionic, andlactic acids. Similarly, water soluble softener pastes which areparticularly suitable for application to textile materials may also beprepared by treating the organic compounds obtained according to theprocesses of the present invention with caustic potash, caustic soda,and similar alkaline materials. Such pastes are usually prepared byheating the compounds to a temperature at which the said compounds areliquid and then adding the said low molecular acid or the alkalinemateriahas the case may be, plus an amount of water-sum cient to obtaina paste of the desired'consistency, and stirring the mixture until asmooth, homogeneous composition is obtained. Organio solvents, such asthe alcohols previously nentioned, may also be added to the softener'past'es to obtain improved solubility.

Illustrative of the preparation of the'di-sub s'tituted amido amidederivatives of dibasic acids are the following illustrative examples.The quantities of all materials employed therein are set forth in partsby weight.

. .Emample 1 276 parts of triple pressed'stearic acid and 104 parts ofhydroxyethyl ethylene diamine are heated together at 180Crwhileiremovingthe waterwhichis formed by their interaction; until theacid value of the reaction mixture is reduced to approximately 5 mgm.KOI-I- per gram. This reaction yields approximately 362 parts of amaterial which consists predominantly of a mixture of materialscorresponding to the two formulas:

The above reaction mixture is kept at 180 C. while 67 partsof diglycolicacid are slowly added thereto. As the diglycolic acid is added, areaction occurs with the evolution of water. After all the diglycolicacid has been added, the temperature of the reaction mixture is raisedto approximately 190 C. and kept at that point until further reactionceases. There is thus obtained approximately 400 parts of materialwhich, at room temperature, is a dark tan, brittle, wax-like material'having an acid value of approximately 30 mgms. KOH per gram and anamine value of approximately 25 mgms. KOH per gram. The reaction productthus obtained comprises predominantly a'mixture of materialscorresponding to the following formulas:

and

n p ep in a fsdftenerflpaste suitable for the treatment of textiles-Q35;parts of the reaction product obtained above are heated with 3 parts of45% caustic potash and G Zparts of water, and themixturestirreduntiluniform. There is obtained, when cool, a Iight tanc IOred,soft paste which is despersible inhotwater. ,When textiles are paddedthrough atextile treating bath containing 1% of this paste,,.thefabricis. made soft to the touch and has excellent draping qualities.This effect is substantially unaffected by washin; or dry cleaning: Whenthis product is applied to dyed fabricsit has no efiect upon the colorshade of thefabriafnor does it produce any deleterious veffection} the,lightlfastness of the u s, n the fabric. t2

The material thus obtained corresponds predominantly to the followingformula:

Thereaction' product obtained abovehas amelting" point of approximately69- C.;" the amine value, as determined by titration,'is 40-50 mgms. KOHper gram.

Depending upon the equipment used and other factors influencing thereaction, it is sometimes necessary to add a 'smalla dditional amount ofphth'alic anhydride "to the reaction mixtureito compensate forphthalicanhydride lost by sublimation, thusinsuring-substantial completion ofthe reaction, --This is likewise truei when using other dicarboxylicacids or derivatives thereof which tend-to distilLsublime o'rdecomposeat the reaction' te' 'peratures" used in the present processes.

The reaction product obtained above may be worked up into a waterdispersible paste by stiracoaser ring 25 parts of the. said reactionproduct with 4 parts of acetic acid and 71 parts of water, thetemperature while mixing being sufiiciently high to cause the reactionproduct to melt. When. cool, the resultant paste is light tan coloredand forms opalescent solutions when dispersed in hot Water. Cottonfabrics or other textile materials upon immersion in a 1% aqueoussolution of this paste, and subsequently dried, have a much softer handthen similar untreated fabrics.

Example 3 276. parts of triple pressed stearic. acid are mixed with 103.parts ofdlethylene triamine and the mixture slowly heated to 130 C.while passing nitrogen therethrough; When the evolution of water ceases,and the acid value of the reaction product. has -dropped toapproximately mgms. KOI-I per gram, there are. then slowly added 110partsfof succinic acid while maintaining the temperature? of thereaction mixture at approximately 185 190!" C. while continuing thepassage of nitrogen through the mixture- After all the succinic acid hasbeenadded, the temwherein R represents the aliphatic residue of coconutfatty acids.

A textile softener paste may be prepared by stirring 20. parts of thereaction product of Ex ample 4 in 80 parts of a 3% tallow soap solution.Textile materials, when treated with an aqueous textile treating bathcontaining a 0.5% solution of the softener paste, acquire a pleasinglysoft feel. This effect is substantially unaffected by washing or drycleaning.

perature is then further raised to 200-2l0 C., Examme 5 r par 5 o byroxyethy ethylene diamine at 552 12 :3 2232 3: fi igg g g g ggg g zlg:1'10 C; until the acid value of the reaction product in i the mnowinfcrmulasj 0 falls to less than 5 mgms. KOH per gram. The

g g temperature of the reaction mixture is held at O H H 170 C. while5.0 grams of anhydrous oxalic acid H 1 are added in small portions.Vigorous agitation 3sf is maintained during the addition of oxalic acid:0 "(3: 5 in order to break the foam which forms. When c addition ofoxalic acid has been completed, the k y" temperature of the reactionmixture is raised to E 190 C. and kept at that point until the reactioncro' 0:0 is substantially completed, as indicated by an l 40 amine valueless than approximately 30 mgms.

g l I I KOH per gram. The reaction product thus obv tained is a lighttan colored wax-like material and having a melting point ofapproximately C.,

l II it CH', CH;NC'CHa CHQ(JNCH2C 2 0 GnHaa-C- HO OH To prepare asoftener paste, 20 parts of the product obtained as described above isheated with 75 parts of water and 5 parts of 4'7 caustic soda, and themixture stirred until homogeneous. When further diluted with water to aconcentration of approximately andapplied to textiles, this productimparts a soft feel to the cloth which is very fast to washing and drycleaning.

Example 4 225 parts of coconut fatty acids are heated with 148 parts ofN,N' dihydroxyethyl ethylene diamine at C. until the acid value of there-,

- action mixture drops to approximately 5 mgms.

KOH per gramor less. The temperature of the reaction mixture is thenraised c0189. (3.,and '74 parts of phthalic anhydride are slowly addedthereto. When the addition of the phthalic anhydride to the reactionmixture has beenpom: pleted, the temperature is further raised 110 200?C. and held at that point until thereaotion is completed. Uponcooling atan colored wax-like and corresponds predominantly to the followingformula:

9: with approximately 15 grams of thesoftener paste per liter ofwater,'and textiles are treated therewith, a very soft, pleasing finishis imparted tothe goods which is not noticeably affected by washing ordry cleaning. Moreover, the finish does not yellow or discolor whitegoods'nor does it deleteriously affect the lightfastness nor the colorshade of dyed fabrics.

Example 6 A concentrated softener paste may be prepared by heating 25parts of the reaction product obtained above with parts oftriethanolamine and 70 parts of water, and stirring the mixture untiluniform. When this paste is 'further diluted with water to aconcentration of approximately 1% to andapplied to textiles,particularly cellulosic textiles, a marked softening action on thefabric is obtained. I r

Example 290 parts of hydrogenatedufish oil fatty acids are heated to 150C. and approximately 90 parts of -70%; ethylene diamine are graduallyintroduced below-the surface of the molten fatty acids. After allthe'amine has; been added the mixture is -slo'wly heated to 170 C.-;andkept at that point until the acid value drops to approximately 10mgrns. 'KOH "per gram. While maintaining tlie-temperati re'of thereaction mixture at 170 C., 120 parts of sebacyl dichloride are slowlyadded'thereto. There .is a-strong evolution of hydrogen chloride duringthis addition. After all the sebacyl dichloride has been added thetemperature is raised to 200 C. while passing nitrogen through themixture. Passage of the nitrogen through the mixture assists in removingthe hydrogen chloride and helps to cause the reaction to go tocompletion more rapidly. The reaction product thus obtained correspondsto the following formula:

= f a7- r i-i -oneom-l a. 1 .3.

' 10 in which R1 and R1 represent'the aliphatic residues ofhydrogenatedfishoil fattyacids. V When the aminevalue of the abovereactio mixture drops to a minimum, the mixture is cooled toapproximately C. .15 parts of 45% caustic potash are then'added thereto,followed by 1500 parts of hot water. The mixture is stirred untiluniform, and is then allowed to cool. There is obtained approximately1900. parts of a light tan colored paste. When this paste isfurtherdiluted'with war'mwater and applied to-textiles, a soft feel is impartedto the textiles; This softening effect is not materially affected by drycleaning or washing.

Emamplet 225 parts of coconut fatty acids and 116 parts of N,Ndiethylethylene diamine are heated together to a temperature of approximately180 C., and the reaction mixture is maintained at that temperature untilthe acid value of the mixture drops to less than approximately 10 mgms.KOI-I per gram. To the resulting reaction product there are added, insmall portions, 72 parts of phthalic anhydride. Upon completion-of theaddition of the phthalicanhydride to the reaction mixture, thetemperature ofjthe' reaction mixture is gradually raised toapproximately 200 C. and

maintained at that point until reaction is substantially completeyas'evidenced by a low amine value. Upon cooling to room temperature, alight, tan colored wax-like material is obtained.

In preparing a softe'nerpaste for the treatment of textiles employingthe'reaction product secured above, the molten reaction product iscooled to a, temperature of approximately C., and

Example 9 288 partsof .caprylic acid are heated to a temperature ofapproximately C., and 74 parts of propylene diamine are graduallyintroduced thereto beneath the surface of the acid. The temperature ofthe mixture is then raised to approximately 180 C. and maintainedthereat until reaction is. substantially"complete; as eviden'ced by an.acid "value 'of less than approximately '10 'mgms. 'KO'I-I per grain.Depending upon the equipment 'used and the conditions lof the reaction,when usin'g"a"relatively volatile amin'a'suchflas propylenediainine, itis often found. that a satisfactorily 'low acidvalue bariot belobtained:b i theluse [ofthe theoretical amount of the amine. In sziich case itis'iieessaryto add'an excess of the amine to 7 compensate for the'aminlos't'by vapor'at'ion. 'Thereac'tion describedabove yield'sapproxiniately- 326 parts or a material-which is. ubs'tantially "of ther61- lowing-formulai- The product thus obtained is dissolved inapproximately 500 parts toluol and reacted therein with 91.5 partshexanedioyl chloride at approximately .85 C. in the presence of ahydrogen chloride acceptor such as pyridine. At completion of thereaction, the reaction mixture is quickly transferred into boiling waterand the mixture is agitated vigorously. Thereafter the water is drawnoff and the toluol removed under vacuum conditions. There is thusobtained approximately 380 parts of a tan, semi-wax-like material,corresponding predominantly to the formula:

The product thus obtained may be dispersed in aqueous solution withcaustic, alkali, or acetic acid in such manner as has been set outhereinbefore to form a softener paste which provides improved drape totextile materials when applied thereto and which has no adverse effecton the lightfastness properties of dyestufis.

Example 276 parts of triple pressed stearic acid are reacted with 104parts of B,B-diaminoethyl ether at 170 C. until the acid value of thereaction mixture drops to less than approximately 5 mgms. KOH per gram.The: temperature of the reaction mixture is then raised to approximately190 C.; then 59 parts of tartaric acid are added thereto in smallportions. The temperature of the reaction mixture is intained at thispoint until a substantially complete reaction has been obtained asindicated by the relatively low amine value of the reaction Product. Thereaction pro uc nsi ts pr domina ly of a compound havin the f rmu Aconcentrated textile softener paste may be prepared by heating parts ofthe product of Example 10 with 75 parts of water and about 5 parts of47% caustic soda, and stirring the mixture until homogeneous.

The hand and texture of textile materials treated with the compounds ofthe present invention are not only greatly improved over those ofuntreated fabrics, but the particular properties imparted to the fabricby the use of such compounds may be varied according to thespecificcompounds employed. For example, those compounds, in which the aliphaticchain portion represented by R1 and R7 in the illustrated eneralformulas is one containing less than 18 carbon atoms, impart exceptionalsoftening elfects to the fabric, while substantial bodying of the fabricwith less softening efiect is had when the compound employed in thetreating bath is one in which the "said .aliphatmradicah consist .ofchains, contaimngimorethan l8 carbon atom The particularly desirableproperties imparted to the textile fabrics bythetrcatment thereof withthe p unds ofiihe present invention are subst n ially p manent d e tothe substan ivity of these compounds toward textile materials. andparticularly towards cellulosic fabrics. Due to the absence of primaryamino groups in the compounds of the presentinvention, there is littledanger of yellowing or discoloration of the fabric under conditionsilofheat; humidity, .or long storage of the goods. JAshas been pointed out,the finishing agents. of the present invention have no effect upon thecolorv shades of dyed fabrics and do not adversely affect thelight'fastne'ss of dyestufis commonly used incoloringftextile :materials. 2 t

While the above products and processes of makingthe same constitutepreferred embodimerits of the present invention, changes may be madetherein without departing from the scope of the invention as defined inthe appended claims.

What is claimed is:

l. A chemical compound corresponding to the formula r( 3-N-[.(C 2)1G]=*CHfir 'N I la 7 s where R1 and R7 are aliphatic chains containing atleast 5 carbon atoms; R2 and Rs represent a radical of the groupconsisting of hydrogen, a lower alkyl radical, and a lower hydroxyalkylradical; R3 and 35 represent a radical of the group consisting ofhydrogen, a lower alkyl radical, a lower hydroxyalkyl radical, and anacyl group containing atleast 6 carbon atoms; G represents a radical ofthe group consisting of an amino group, a lower alkyl substituted aminogroup, a lower alkylol substituted amino group, oxygen and sulfur; a andc represent integers from 0 to 6; End e and [represent integers from 1to 6; X represents a dicarboxylic acid residue in which R4 represents amember of the group consisting of aliphatic, cyclo aliphatic, aromatic,andall;ylaromatic groups; and any of the said groups containing in theirstructure a member ofthe class consisting of halogen, oxygen, and sulfuratoms, and amino, ester, hydroxyl and ether groups.

2. A chemical compound corresponding to the formula I v 0- R2 a R;

a 't-t-(oHal-nfl where R1 and Prime aliphatic chains containing at least5 carbon atoms; R2 and Re represent a radical of the group consisting ofhydrogen, a lower alkyl radical, and a lower hydroxyalkyl radical; R3and R5 represent a radical of the represents a dicarboxylic acid residuein which groupconsisting of hydrogen, a lower alkyl radical, a lowerhydroxyalkyl radical, and an acyl group containing, at least 6 carbonatoms; band d represent integers from 1 to 6; and where X where R1 andR1 are aliphatic chains containing'at least 5 carbon atoms; R2 and Rsrepresent a radical of the group consisting of hydrogen, a lower alkylradical, and a lower hydroxyalkyl radical; R3 and R5 represent a radicalof the group consisting of hydrogen, a lower alkyl radical, a lowerhydroxyalkyl radical, and an acyl group containing atleast. 6 carbonatoms; G represents a radical of the group consisting of an amino group,a lower alkyl substituted amino group, a lower alkylol substituted aminogroup, oxygen and sulfur; where a and 0 represent integers from 1 to 6;and where X representsa dicarboxylic acid residue in which R4 representsa member of the group consisting of aliphatic, cyclo aliphatic,aromatic, and alkyl aromatic group; and any of the said groupscontaining in their structure a member of the class consisting ofhalogen, oxygen, and sulfur atoms, and amino, ester, hydroxyl and ethergroups.

4. Chemical compounds corresponding to the where R. is an aliphaticchain containing at least 5 carbon atoms.

5. Chemical compounds corresponding to the formula where R is analiphatic chain containing at least 5 carbon atoms.

- Chemical.compounds oi responding' to the formula I R C N C2H4' NC2H4OH r where R is an aliphatic chain containing at -1east 5 carbonatoms.

7. Chemical compounds corresponding to the formula where R is analiphatic chain containing at least ficarbonatomsj 8. Chemical compoundscorresponding .to the formula i r IBCNV-CZH4N =0 ($112 v 'RfiNC2H4-' Iwhere R is an aliphatic chain containing at least 5 carbon atoms.

9. A process for the preparation of a disubstituted amido amidederivative of a disbasic acid which comprises reacting the condensationproduct of an aliphatic carboxylic acid containing at least 6 carbonatoms and a polyamine, said condensation product containing at least oneamino group which contains free hydrogen, at a temperature betweenapproximately C. to 210 C. with a member of the group consisting ofaliphatic dicarboxylic acids containing at least 3 carbon atoms,aromatic dicarboxylic acids, alkyl aromatic dicarboxylic acids, cyclicaliphatic dicarboxylic acids, and anhydrides, esters, and acyl halidesthereof.

10. A process for the preparation of a disubstituted amido amidederivative of a dibasic acid which comprises reacting an aliphaticcarboxylic acid containing at least 6 carbon atoms with a polyamine at atemperature of 150 C. to 180 C.

cyclic aliphatic dicarboxylic acids, and anhydrides, esters and acylhalides thereof.

11. A process for the preparation of a climbstituted amido amidederivative of a dibasic acid which comprises reacting the condensationproduct of an aliphatic carboxylic acid containing at least 6 carbonatoms and a polyamine, said condensation product having not more thanone primary amino group, at a temperature between approximately 150 C.to 210 C. with a member of the group consisting of aliphaticdicarboxylic acids containing at least 3 carbon atoms, aromaticdicarboxylic acids, alkyl aromatic dicarboxylic acids, cyclic aliphatic'dicarboxylic acids, and anhydrides, esters, and acyl halides thereof,to form a condensation "product *free of primary amino groups.

12. -A process for the preparation of a disubstituted amido amidederivative of a-dibasicacid which comprises reacting an aliphaticcarboxylic acid containing at leastfi carbon atoms with a polyamine at atemperature of 150 C. to 180 C. to form a condensation product havingnot more than one primary amino group, and thereafter reacting saidcondensation product at a temperature between approximately 150 C. to210 C. with a member of the group consisting of aliphatic dicarboxylicacids containing at least 3 carbon atoms, aromatic dicarboxylic acids,alkyl aromatic dicarboxylic acids, cyclic aliphatic dicarboxylic acids,and anhydrides, esters, and acyl halides thereof, to form a condensationproduct free of primary amino groups.

13. A process for the preparation :of .a disubstituted amido amidederivative of'adibasic acid. which comprises reacting thecondensation'product of an aliphatic carboxylic acid containing at least6 carbon atoms and aipolyamine, said condensation product having noprimary amino groups and not more than one secondary amino group; -.-ata temperature between approximately C. to 210:C. withxa member of thegroup consisting of aliphatic dicarboxylic acids containing at least3:carbo'n atomsaroma'tic dicarboxylic acids; alizyl'aromaticdicarboxylic acids, cyclic aliphatic dicarboxylic acids, and anhydrides,esters and acyl halides thereof, to form a condensation product free ofprimary and secondary groups. i 3

14. -A process for the preparation .of .a .disubstituited amide amidederivative of a dibasic acid which comprises reacting an aliphaticcarboxylic acid containing at least 6 carbon atoms with a polyamine at atemperature of 150 C. to C. to form a condensation product having noprimary amino groups and not more than one sec ondary amino group, andthereafter reacting said condensation product at a temperature betweenapproximately 150 C. to 210 C. with a member-of the group consisting ofaliphatic dicarboxylic acids containing at least 3 carbon atoms,aromatic dicarboxylic acids, alkyl aromatic dicarboxylic acids, cyclicaliphatic dicar- 'boxylic acids, and an'hydrides, esters, and acylhalides'thereof, to form a condensation product free of primary andsecondary amino groups.

' HERMAN B. GOLDSTEIN.

STANLEY I. CLARY.

I REFERENCES CITED TheJfollowing references are .of record in the file"of .this patent:

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3 393 Robinson-ct a1 Aug. 12,1:19 i7

1. A CHEMICAL COMPOUND CORRESPONDING TO THE FORMULA 